Allyl Alcohol → 3-(4-Acetamidophenyl)propanal

Participants

Reaction Steps

To a mixture of N-(4-Iodophenyl)acetamide (10.8 g, 42 mmol, 1.0 equiv) and DMF (50.0 ml) were added tetrabutylammonium chloride (11.7 g, 42 mmol, 1.0 equiv), NaHCO3 (8.7 g, 105 mmol), and allyl alcohol (4.2 ml, 63 mmol, 1.5 equiv) and the mixture was stirred for 10 min. To the resulting mixture PdCl2 (1.21 g, 9.6 mmol, 0.23 equiv) was added and the mixture was stirred under nitrogen for 45 h. The resulting mixture was extracted with EtOAc (3×100 ml). The combined extracts were washed with 5% HCl, brine, dried over MgSO4 and concentrated under vacuum. The residue was purified by column chromatography (EtOAc:hexane 70:30) to give 3-(4′-Acetamidophenyl)-1-propanal (1.92 g, 23.1%) which was used as such in the next step.

Provenance & Evidence